TitleStructural revision of sesbagrandiflorains A and B, and synthesis and biological evaluation of 6-methoxy-2-arylbenzofuran derivatives.
Publication TypeJournal Article
Year of Publication2021
AuthorsNoviany N, Samadi A, Carpenter EL, Abugrain ME, Hadi S, Purwitasari N, Indra G, Indra A, Mahmud T
JournalJ Nat Med
Volume75
Issue1
Pagination66-75
Date Published2021 Jan
ISSN1861-0293
KeywordsBenzofurans, Humans, Molecular Structure
Abstract

Sesbagrandiflorains A (1) and B (2), isolated from the stem bark of the Indonesian fabaceous plant Sesbania grandiflora, were reported to be 6-methoxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1-benzofuran-3-carbaldehyde and 6-hydroxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1-benzofuran-3-carbaldehyde, respectively. However, based on reevaluation of their 1D and 2D NMR data, the chemical structures of 1 and 2 have been revised to 4-hydroxy-2-(4´-hydroxy-2´-methoxyphenyl)-6-methoxybenzofuran-3-carbaldehyde and 4-hydroxy-2-(4´-hydroxy-2´-hydroxyphenyl)-6-methoxybenzofuran-3-carbaldehyde, respectively. In addition, seven new derivatives of 1 have been synthesized from the natural product in good yields (65 - 93%). The chemical structures of the synthetic compounds-one diester (6), four ethers (7-10), one secondary amine (11), and one oxime (12)-were confirmed by MS and NMR analysis. Compound 6 exhibited moderate antibacterial activity against the plant pathogen Rhodococcus fascians with a MIC of 0.1 mg/mL. Compounds 8 and 12 demonstrated respectable cytotoxicity against A375 melanoma cancer cells line with the relative IC values of 22.8 and 32.7 μM, respectively.

DOI10.1007/s11418-020-01445-2
Alternate JournalJ Nat Med
PubMed ID32809097
PubMed Central IDPMC7791000
Grant ListPSN Grant 2017-2019 (No. 860/UN26.21/PN/2019), PDUPT Grant 2019 (No. 856/UN26.21/PN/2019) and World Class Professor Program-Scheme B 2018 (No.123.44/D2.3/KP/2018) / / the Directorate of Research and Community Services, Directorate General of Higher Education, The Ministry of Research, Technology and Higher Education, Republic of Indonesia /
T32AT010131 / / the National Center for Complementary & Integrative Health of the National Institutes of Health /
2014-51181-22384 / / the National Institute of Food and Agriculture of the U.S. Department of Agriculture /
#2014162 / / M.J. Murdock Charitable Trust (US) /
HEI Grant 1S10OD018518 / / Foundation for the National Institutes of Health /
S10 OD018518 / OD / NIH HHS / United States
T32 AT010131 / AT / NCCIH NIH HHS / United States